Journal
NATURE COMMUNICATIONS
Volume 6, Issue -, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/ncomms8204
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Funding
- National Basic Research Program of China (973 Program) [2010CB833200]
- NSFC [21172100, 21272105, 21290183]
- Program for Changjiang Scholars and Innovative Research Team in University [PCSIRT: IRT1138]
- FRFCU [lzujbky-2013-ct02]
- '111' Program of MOE
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The structurally complex alkaloid gelsemine was previously thought to have no significant biological activities, but a recent study has shown that it has potent and specific antinociception in chronic pain. While this molecule has attracted significant interests from the synthetic community, an efficient synthetic strategy is still the goal of many synthetic chemists. Here we report the asymmetric total synthesis of (+)-gelsemine, including a highly diastereoselective and enantioselective organocatalytic Diels-Alder reaction, an efficient intramolecular trans-annular aldol condensation furnishing the prolidine ring and establishing the configuration of the C20 quaternary carbon stereochemical centre. The entire gelsemine skeleton was constructed through a late-stage intramolecular S(N)2 substitution. The enantiomeric excess of this total synthesis is over 99%, and the overall yield is around 5%.
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